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Effect of alkyl chain length and linker atom on the crystal packing in 6,12-dialkoxy- and 6,12-dialkylsulfanyl-benzo[1,2-b:4,5-b’]bis[b]benzothiophenes

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journal contribution
posted on 05.08.2019 by Shahzad Riaz, Mark Edgar, Mark Elsegood, Lynne Horsburgh, Simon J Teat, Thomas G Warwick, George Weaver
The effect of varying the chain length on the solid state conformation and packing of 6,12-dialkoxy- and 6,12-dialkylsulfanyl-benzo[1,2-b:4,5-b’]bis[b]benzothiophenes has been studied. The compounds were prepared by SNAr reaction of 6,12-difluorbenzo[1,2-b:4,5-b’]bis[b]benzothiophene with alkoxides or alkanethiolates derived from C7-C10 alcohols and alkanethiols. Single crystal X-ray diffraction analysis revealed all but two compounds to crystallise in the triclinic space group P1. Two compounds were obtained as monoclinic crystals with space group P21/c. The alkoxy substituted compounds adopted a molecular conformation with a step from the core and a gauche conformation about the C1’-C2’ bond placing the alkyl chains close to parallel with the pentacyclic arene ring system, whereas in the alkylsufanyl derivatives, the alkyl chains were arranged strongly deviated from the plane of the ring, with the sulfur atom anti-periplanar to C3’ of the alkyl chain. NMR measurement of T1 relaxation in CDCl3 showed both the alkoxy and alkylsulfanyl substituents to be freely rotating at ambient temperature in solution indicating the orientation of the chains in the solid state was due to packing interactions during crystallization.

Funding

The Advanced Light Source is supported by the Director, Office of Science, Office of Basic Energy Sciences, of the U.S. Department of Energy under Contract No. DE-AC02-05CH11231.

History

School

  • Science

Department

  • Chemistry

Published in

Crystal Growth & Design

Volume

19

Issue

9

Pages

5237 - 5248

Publisher

American Chemical Society (ACS)

Version

AM (Accepted Manuscript)

Rights holder

© American Chemical Society

Publisher statement

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Crystal Growth & Design, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.cgd.9b00644

Acceptance date

22/07/2019

Publication date

2019-07-22

Copyright date

2019

ISSN

1528-7483

eISSN

1528-7505

Language

en

Depositor

Dr George Weaver

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